Lithium hydroxide, monohydrate → (S)-13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid

HRID 2201718Notes

Reaction equation

HRID 2201718 reaction equation
[CH2:1]([C@@H:5]([C:22](=[O:29])[NH:23][CH2:24][C:25]([O:27]C)=[O:26])[NH:6][C:7](=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:2]([CH3:4])[CH3:3].O[Li].O>C1COCC1.O>[CH2:1]([C@@H:5]([C:22](=[O:29])[NH:23][CH2:24][C:25]([OH:27])=[O:26])[NH:6][C:7](=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712539(S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate

Product 1

HCID 86712540(S)-13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oate (6w) in THF was added a solution of LiOH.H2O in water at room temperature. After 3 h, the reaction mixture was concentrated, diluted with water and acidified with a 1N aqueous solution of HCl to about pH 4-5. The mixture was stirred for 15 min and the white precipitate formed was filtered off, rinsed with water, and dried to afford (S)-13-isobutyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid (7w).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water
  3. customthe white precipitate formed
  4. filtrationwas filtered off
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-ac67f9e9dd304a16a5875a1d9795987d
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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